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US 2014/0235850 A1Published application
Synthesis of hmo core structures
AssigneeGlycom A/S
InventorsImre Kovács, István Bajza, Markus Hederos, Gyula Dekany, Sándor Demkó, Nikolay Khanzhin
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Abstract
The invention relates to a method for making precursors of HMO core structures comprising a step of reacting an N-acetyllactosamine or lacto-N-biose derivative donor with a lactose or N-acetyllactosamine derivative acceptor, wherein the donor is an oxazoline donor.
Claims20
A method for making a precursor of an HMO core structure comprising a step of reacting a disaccharide glucosamine donor of formula 1
- wherein X is a halogen atom selected from the group consisting of F, Cl, Br and I, n is 0, 1, 2 or 3, and one of the R1-groups is a residue of formula A
- and the other R1-group is acyl, and R2 and R3 are independently acyl, with an acceptor of formula 2
- wherein R4 is acyl, R5 is selected from the group consisting of H, a peracylated N-acetyllactosaminyl residue and a peracylated lacto-N-biosyl residue, R6 is H or acyl, R7 is selected from the group consisting of H, acyl, acetal type groups, silyl and a peracylated N-acetyllactosaminyl residue optionally substituted with 1 or 2 moieties selected from a peracylated N-acetyllactosaminyl group and a lacto-N-biosyl group, R8 is a group removable by hydrogenolysis, Y is —OR4 or acetylamino optionally substituted by a halogen atom, Q is a bond when Y is —R4 and Q is a carbohydrate linker comprising a peracylated lactose moiety optionally substituted either with a peracylated N-acetyllactosaminyl residue or a peracylated lacto-N-biosyl residue when Y is an acetylamino optionally substituted by a halogen atom, provided that at least one of R5 and R7 is H,
- in the presence of a boron halogenide promoter.
1 more element
A compound of formula 3′
- wherein R4′ is a low-migrating acyl group, R6 is H or acyl, R8 is a group removable by hydrogenolysis, Y is —OR4′ or acetylamino optionally substituted by a halogen atom, Q is a bond when Y is —OR4′ and Q is a carbohydrate linker comprising a peracylated lactose moiety optionally substituted with either a peracylated N-acetyllactosaminyl residue or a peracylated lacto-N-biosyl residue when Y is an acetylamino optionally substituted by a halogen atom, R9 is selected from the group consisting of a residue of formula B, a peracylated N-acetyllactosaminyl residue and a peracylated lacto-N-biosyl residue and R10 is selected from the group consisting of a residue of formula B, acyl, acetal type groups, silyl and a peracylated N-acetyllactosaminyl residue optionally substituted with 1 or 2 moieties selected from a peracylated N-acetyllactosaminyl group or a peracylated lacto-N-biosyl group, provided that at least one of R9 and R10 is a residue of formula B
- wherein X is a halogen atom selected from the group consisting of F, Cl, Br and I, n is 0, 1, 2 or 3, and one of the R1-groups is a residue of formula A
- and the other R1-group is acyl, R2 and R3 are independently acyl.
A compound of formula 2B
- wherein R4 is acyl and R8 is a group removable by hydrogenolysis.
Dependencies are inferred from the claim text.